Water → HCID 19806397, compound

HRID 1681342Notes

Reaction equation

HRID 1681342 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[NH2:16][CH2:17][CH:18]([OH:27])[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.O>CO>[OH:9][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH:8]([NH:16][CH2:17][CH:18]([OH:27])[CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 185583(R,R)-Stilbene oxideHCID 19806408HCID 19806408, compound

Product 1

HCID 19806397HCID 19806397, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-stilbene oxide (1.96 g, 0.010 mol) and 4-(4-amino-3-hydroxybutyl)morpholine (3.48 g, 0.020 mol) was heated on a steam bath for 18 hours. The resulting viscous oil was dissolved in methanol (20 mL) and the solution poured into water (150 mL). The aqueous mixture was extracted twice with 100 mL portions of methylene chloride. The extract was dried (MgSO4) and concentrated to obtain 3.29 g of the impure product as an oil. The material was chromatographed on silica gel (60 g) using increasing portions of acetone in ethyl acetate to elute the product. After combining the desired fractions and concentration under vacuum, 2.21 g (67%) of the product was obtained. The product was purified and characterized as the cyclohexyl sulfamic acid salt, mp 159°-160° C. (methanol/isopropyl ether).

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. extractionThe aqueous mixture was extracted twice with 100 mL portions of methylene chloride
  3. dry with materialThe extract was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bbe0fdaf7fb74b5a9d13d99f5ce2b8bc
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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